Triethylamine → HCID 13745139, compound

HRID 2267011Notes

Reaction equation

HRID 2267011 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].C(N(CC)CC)C.[CH3:22][N:23]([CH3:27])[C:24](Cl)=[S:25]>ClCCl>[C:12]([C:3]1[CH:4]=[CH:5][C:6]([O:11][C:24](=[S:25])[N:23]([CH3:27])[CH3:22])=[C:7]([CH2:8][CH2:9][CH3:10])[C:2]=1[OH:1])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27871Dimethylthiocarbamoyl chlorideHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 13745139HCID 13745139, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a mixture of 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (2 g, 10.3 mmol), triethylamine (1.6 mL 11.3 mmol), and dichloromethane (40 mL) at room temperature. Add dimethylthiocarbamoyl chloride (1.27 g, 10.3 mmol) and stir at room temperature overnight. Wash the mixture with 1M hydrochloric acid (25 mL), dry over magnesium sulfate, filter and concentrate. Purify the residue via silica chromatography eluting with hexanes to 7:3 hexanes:ethyl acetate to afford dimethyl-thiocarbamic acid O-(4-acetyl-3-hydroxy-2-propyl-phenyl) ester (1.2 g, 41%) as a light yellow solid. Stir the yellow solid in tetradecane (10 mL) at 250° C. for an hour and purify by silica chromatography eluting with hexanes to 6:4 hexanes:ethyl acetate to give the title compound (1.08 g, 90%) as a white solid. LCMS (m/z) 280 m−1.

Workup

  1. washWash the mixture with 1M hydrochloric acid (25 mL)
  2. dry with materialdry over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue via silica chromatography
  6. washeluting with hexanes to 7:3 hexanes

Sources & evidence

ORD record
ord-9c6e1485a11642a2acb0d3dd28fe14c7
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

Loading…